Herbicidal sulphonylamino(thio)carbonyl triazolin(thi)ones with heterocyclyl(alk)oxy substituents

ABSTRACT

The novel title compounds of the formula (I) ##STR1## in which Q 1  represents oxygen or sulphur, 
     Q 2  represents oxygen or sulphur, 
     R 1  represents hydrogen, hydroxyl, amino or alkylideneamino or represents an in each case optionally substituted radical from the series consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl, 
     R 2  represents in each case optionally substituted heterocyclyl or heterocyclylalkyl, and 
     R 3  represents an in each case optionally substituted radical from the series consisting of alkyl, aralkyl, aryl and heteroaryl, 
     and salts of compounds of the formula (I), processes and novel intermediates for their preparation, and their use as herbicides.

This application is a 371 of PCT/EP96/02933 filed Jul. 4, 1996.

The invention relates to novelsulphonylamino(thio)carbonyltriazolin(thi)ones havingheterocyclyl(alk)oxy substituents, to a number of processes and to novelintermediates for their preparation, and to their use as herbicides.

It is already known that certain sulphonylaminocarbonyltriazolinonespossess herbicidal properties (cf. EP-341 489, EP-A 422 469, EP-A 425948, EP-A 431 291, EP-A 507 171). The action of these compounds,however, is not in every respect satisfactory.

The novel sulphonylamino(thio)carbonyltriazolin(thi)ones havingheterocyclyl(alk)oxy substituents have now been found of the generalformula (I) ##STR2## in which Q¹ represents oxygen or sulphur,

Q² represents oxygen or sulphur,

R¹ represents hydrogen, hydroxyl, amino or alkylideneamino or representsan in each case optionally substituted radical from the seriesconsisting of alkyl, alkenyl, alkinyl, alkoxy, alkenytoxy, alkylamino,dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl,cycloalkylamino, aryl and arylalkyl,

R² represents in each case optionally substituted heterocyclyl orheterocyclylalkyl, and

R³ represents an in each case optionally substituted radical from theseries consisting of alkyl, aralkyl, aryl and heteroaryl, and salts ofcompounds of the formula (I).

The novel sulphonylamino(thio)carbonyltriazolin(thi)ones havingheterocyclyl(alk)oxy substituents, of the general formula (I), areobtained if

(a) triazolin(thi)ones of the general formula (II) ##STR3## in which Q¹,R¹ and R² have the meanings given above are reacted with sulphonyliso(thio)cyanates of the general formula (III)

    R.sup.3 --SO.sub.2 --N═C═Q.sup.2                   (III)

in which

Q² and R³ have the meanings given above, optionally in the presence of areaction auxiliary and optionally in the presence of a diluent, or if

(b) triazolin(thi)one derivatives of the general formula (IV) ##STR4##in which Q¹, Q², R¹ and R² have the meanings given above and

Z represents halogen, alkoxy, aralkoxy or aryloxy are reacted withsulphonamides of the general formula (V)

    R.sup.3 --SO.sub.2 --NH.sub.2                              (V)

in which

R³ has the meaning given above, optionally in the presence of an acidacceptor and optionally in the presence of a diluent,

or if

(c) triazolin(thi)ones of the general formula (II) ##STR5## in which Q¹,R¹ and R² have the meanings given above are reacted with sulphonamidederivatives of the general formula (VI)

    R.sup.3 --SO.sub.2 --NH--CQ.sup.2 --Z                      (VI)

in which

Q² and R³ have the meanings given above and

Z represents halogen, alkoxy, aralkoxy or aryloxy, optionally in thepresence of an acid acceptor and optionally in the presence of adiluent,

or if

(d) triazolin(thi)ones of the general formula (II) ##STR6## in which Q¹,R¹ and R² have the meanings given above are reacted with sulphonylhalides of the general formula (VII)

    R.sup.3 --SO.sub.2 --X                                     (VII)

in which

R³ has the meaning given above and

X represents halogen and with metal (thio)cyanates of the generalformula (VIII)

    MQ.sup.2 CN (VIII)

in which

Q² has the meaning given above and

M represents an alkali metal or alkaline earth metal equivalent,optionally in the presence of a reaction auxiliary and optionally in thepresence of a diluent,

and if desired the compounds of the formula (I) obtained by process (a),(b), (c) or (d) are converted into salts by customary methods.

The novel sulphonylamino(thio)carbonyltriazolin(thi)ones havingheterocyclyl(alk)oxy substituents, of the general formula (I), aredistinguished by a strong herbicidal activity.

The invention relates preferably to compounds of the formula (I) inwhich

Q¹ represents oxygen or sulphur,

Q² represents oxygen or sulphur,

R¹ represents hydrogen, hydroxyl, amino or C₁ -C₆ -alkylideneamino, orrepresents optionally fluoro-, chloro-, bromo-, cyano-, C₁ -C₄ -alkoxy-,C₁ -C₄ -alkylcarbonyl- or C₁ -C₄ -alkoxy-carbonyl-substituted C₁ -C₆-alkyl, or represents in each case optionally fluoro-, chloro- and/orbromo-substituted C₂ -C₆ -alkenyl or C₂ -C₆ -alkinyl, or represents C₁-C₆ -alkyloxy or C₃ -C₆ -alkenyloxy, or represents in each caseoptionally fluoro- and/or chloro-substituted C₁ -C₆ -alkylamino, di-(C₁-C₄ -alkyl)-amino or C₁ -C₄ -alkanoylamino, or represents in each caseoptionally fluoro-, chloro-, bromo- and/or C₁ -C₄ -alkyl-substituted C₃-C₆ -cycloalkyl or C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, or represents ineach case optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C₁ -C₄-alkyl-, trifluoromethyl-, C₁ -C₄ -alkoxy- and/or C₁ -C₄-alkoxy-carbonyl-substituted phenyl or phenyl-C₁ -C₄ -alkyl,

R² represents in each case optionally halogeno- and/or C₁ -C₄-alkyl-substituted oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl,tetrahydrothienyl, pyridyl, pyrimidyl, oxetanyl-C₁ -C₄ -alkyl,thietanyl-C₁ -C₄ -alkyl, furyl-C₁ -C₄ -alkyl, tetrahydrofuryl-C₁ -C₄-alkyl, thienyl-C₁ -C₄ -alkyl, tetrahydrothienyl-C₁ -C₄ -alkyl,pyridyl-C₁ -C₄ -alkyl or pyrimidyl-C₁ -C₄ -alkyl, and

R³ represents the group ##STR7## in which R⁴ and R⁵ are identical ordifferent and represent hydrogen, fluoro, chloro, bromo, iodo, nitro orC₁ -C₆ -alkyl (which is optionally substituted by fluoro, chloro, bromo,cyano, carboxyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylamino-carbonyl,di-(C₁ -C₄ -alkyl)-amino-carbonyl, hydroxyl, C₁ -C₄ -alkoxy, formyloxy,C₁ -C₄ -alkyl-carbonyloxy, C₁ -C₄ -alkoxy-carbonyloxy, C₁ -C₄-alkylamino-carbonyloxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁-C₄ -alkylsulphonyl, di-(C₁ -C₄ -alkyl)-amino-sulphonyl, C₃ -C₆-cycloalkyl or phenyl), or represent C₂ -C₆ -alkenyl (which isoptionally substituted by fluoro, chloro, bromo, cyano, C₁ -C₄-alkoxy-carbonyl, carboxyl or phenyl), or represent C₂ -C₆ -alkinyl(which is optionally substituted by fluoro, chloro, bromo, cyano, C₁ -C₄-alkoxy-carbonyl, carboxyl or phenyl), or represent C₁ -C₄ -alkoxy(which is optionally substituted by fluoro, chloro, bromo, cyano,carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁-C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl), or represent C₁ -C₄-alkylthio (which is optionally substituted by fluoro, chloro, bromo,cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulphinyl or C₁ -C₄ -alkylsulphonyl), or represent C₂ -C₆-alkenyloxy (which is optionally substituted by fluoro, chloro, bromo,cyano or C₁ -C₄ -alkoxy-carbonyl), or represent C₂ -C₆ -alkenylthio(which is optionally substituted by fluoro, chloro, bromo, cyano, nitro,C₁ -C₃ -alkylthio or C₁ -C₄ -alkoxy-carbonyl), C₃ -C₆ -alkinyloxy or C₃-C₆ -alkinylthio, or represent the radical --S(O)_(P) --R⁶, where

p represents the numbers 1 or 2 and

R⁶ represents C₁ -C₄ -alkyl (which is optionally substituted by fluoro,chloro, bromo, cyano or C₁ -C₄ -alkoxy-carbonyl), C₃ -C₆ -alkenyl, C3-C₆-alkinyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄ -alkylamino, C₁ -C₄-alkylamino, di-(C₁ -C₄ -alkyl)-amino or phenyl or represents theradical --NHOR⁷, where

R⁷ represents C₁ -C₁₂ -alkyl (which is optionally substituted by fluoro,chloro, cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkyl-carbonyl, C₁ -C₄-alkoxycarbonyl, C₁ -C₄ -alkylamino-carbonyl or Di-(C₁ -C₄-alkyl)-amino-carbonyl), or represents C₃ -C₆ -alkenyl (which isoptionally substituted by fluoro, chloro or bromo), C₃ -C₆ -alkinyl, C₃-C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₂ -alkyl or phenyl-C₁ -C₂-alkyl (which is optionally substituted by fluoro, chloro, nitro, cyano,C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxycarbonyl), or representsbenzhydryl or represents phenyl (which is optionally substituted byfluoro, chloro, nitro, cyano, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄-alkoxy, C₁ -C₂ -fluoroalkoxy, C₁ -C₄ -alkylthio, trifluoromethylthio orC₁ -C₄ -alkoxy-carbonyl),

R⁴ and/or R⁵ additionally represent phenyl or phenoxy, or represent C₁-C₄ -alkylcarbonylamino, C₁ -C₄ -alkoxy-carbonylamino, C₁ -C₄-alkylamino-carbonyl-amino or di-(C₁ -C₄ -alkyl)-amino-carbonylamino, orrepresent the radical --CO--R⁸, where

R⁸ represents hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆-alkoxy, C₃ -C₆ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₁ -C₄ -alkylthio, C₁-C₄ -alkylamino, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl-aminoor di-(C₁ -C₄ -alkyl)-amino (which are optionally substituted by fluoroand/or chloro),

R⁴ and/or R⁵ additionally represent trimethylsilyl, thiazolinyl, C₁ -C₄-alkylsulphonyloxy or di-(C₁ -C₄ -alkyl)-aminosulphonylamino orrepresent the radical

    --CH═N--R.sup.9,

where

R⁹ represents optionally fluoro-, chloro-, cyano-, carboxyl-, C₁ -C₄-alkoxy-, C₁ -C₄ -alkylthio-, C₁ -C₄ -alkylsulphinyl- or C₁ -C₄-alkylsulphonyl-substituted C₁ -C₆ -alkyl, or represents optionallyfluoro- or chloro-substituted benzyl, or represents optionally fluoro-or chloro-substituted C₃ -C₆ -alkenyl or C₃ -C₆ -alkinyl, or representsoptionally fluoro-, chloro-, bromo-, C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy-,trifluoromethyl-, trifluoromethoxy- or trifluoromethylthio-substitutedphenyl, or represents optionally fluoro- and/or chloro-substituted C₁-C₆ -alkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkinyloxy or benzyloxy, orrepresents amino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino,phenylamino, C₁ -C₄ -alkyl-carbonylamino, C₁ -C₄ -alkoxycarbonylamino orC₁ -C₄ -alkyl-sulphonylamino or represents optionally fluoro-, chloro-,bromo- or methyl-substituted phenylsulphonylamino,

and also

R³ represents the radical ##STR8## in which R¹⁰ represents hydrogen orC₁ -C₄ -alkyl,

R¹¹ and R¹² are identical or different and represent hydrogen, fluoro,chloro,bromo, nitro, cyano, C₁ -C₄ -alkyl (which is optionallysubstituted by fluoro and/or chloro), C₁ -C₄ -alkoxy (which isoptionally substituted by fluoro and/or chloro), carboxyl, C₁ -C₄-alkoxy-carbonyl, dimethylaminocarbonyl, C₁ -C₄ -alkylsulphonyl ordi-(C₁ -C₄ -alkyl)-aminosulphonyl;

and also

R³ represents the radical ##STR9## in which R¹³ and R¹⁴ are identical ordifferent and represent hydrogen, fluoro, chloro, bromo, nitro, cyano,C₁ -C₄ -alkyl (which is optionally substituted by fluoro and/or chloro)or C₁ -C₄ -alkoxy (which is optionally substituted by fluoro and/orchloro);

and also

R³ represents the radical ##STR10## in which R¹⁵ and R¹⁶ are identicalor different and represent hydrogen, fluoro, chloro, bromo, nitro,cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluoro and/orchloro), C₁ -C₄ -alkoxy (which is optionally substituted by fluoroand/or chloro), or represent C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinylor C₁ -C₄ -alkylsulphonyl (which are optionally substituted by fluoroand/or chloro) or represent aminosulphonyl or mono-(C₁ -C₄-alkyl)-aminosulphonyl, or represent di-(C₁ -C₄ -alkyl)-aminosulphonylor C₁ -C₄ -alkoxy-carbonyl or dimethylaminocarbonyl;

and also

R³ represents the radical ##STR11## in which R¹⁷ and R¹⁸ are identicalor different and represent hydrogen, fluoro, chloro, bromo, C₁ -C₄-alkyl (which is optionally substituted by fluoro and/or bromo) or C₁-C₄ -alkoxy (which is optionally substituted by fluoro and/or chloro),or represent C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄-alkylsulphonyl (which are optionally substituted by fluoro and/orchloro), or represent di-(C₁ -C₄ -alkyl)-aminosulphonyl;

and also

R³ represents the radical ##STR12## in which R¹⁹ and R²⁰ are identicalor different and represent hydrogen, fluoro, chloro, bromo, cyano,nitro, C₁ -C₄ -alkyl (which is optionally substituted by fluoro and/orchloro), C₁ -C₄ -alkoxy (which is optionally substituted by fluoroand/or chloro), C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄-alkylsulphonyl (which are optionally substituted by fluoro and/orchloro), di-(C₁ -C₄ -alkyl)-amino-sulphonyl, C₁ -C₄ -alkoxy-carbonyl ordimethylaminocarbonyl, and

A represents oxygen, sulphur or the group N-Z¹, where

Z¹ represents hydrogen, C₁ -C₄ -alkyl (which is optionally substitutedby fluoro, chloro, bromo or cyano), C₃ -C₆ -cycloalkyl, benzyl, phenyl(which is optionally substituted by fluoro, chloro, bromo or nitro), C₁-C₄ -alkylcarbonyl, C₁ -C₄ -alkoxycarbonyl or di-(C₁ -C₄-alkyl)-aminocarbonyl;

and also

R³ represents the radical ##STR13## in which R²¹ and R²² are identicalor different and represent hydrogen, C₁ -C₄ -alkyl, halogen, C₁ -C₄-alkoxy-carbonyl, C₁ -C₄ -alkoxy or C₁ -C₄ -halogenoalkoxy,

Y¹ represents sulphur or the group N-R²³, where

R²³ represents hydrogen or C₁ -C₄ -alkyl;

and also

R³ represents the radical ##STR14## in which R²⁴ represents hydrogen, C₁-C₄ -alkyl, benzyl, pyridyl, quinolyl or phenyl,

R²⁵ represents hydrogen, halogen, cyano, nitro, C₁ -C₄ -alkyl (which isoptionally substituted by fluoro and/or chloro), C₁ -C₄ -alkoxy (whichis optionally substituted by fluoro and/or chloro), dioxolanyl or C₁ -C₄-alkoxy-carbonyl, and

R²⁶ represents hydrogen, halogen or C₁ -C₄ -alkyl.

The invention additionally relates preferably to sodium salts and topotassium, magnesium, calcium, ammonium, C₁ -C₄ -alkyl-ammonium, di-(C₁-C₄ -alkyl)-ammonium, tri-(C₁ -C₄ -alkyl)-ammonium, tetra-(C₁ -C₄-alkyl)-ammonium, tri-(C₁ -C₄ -alkyl)-sulphonium, C₅ - or C₆-cycloalkyl-ammonium and di-(C₁ -C₂ -alkyl)-benzyl-ammonium salts ofcompounds of the formula (I) in which Q¹, Q², R¹, R² and R³ have themeanings given above as preferred.

The invention relates in particular to compounds of the formula (I) inwhich

Q¹ represents oxygen or sulphur,

Q² represents oxygen or sulphur,

R¹ represents in each case optionally fluoro-, chloro-, cyano-, methoxy-or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, or represents in each case optionally fluoro-, chloro- orbromo-substituted propenyl, butenyl, propinyl or butinyl, or representsmethoxy, ethoxy, n- or i-propoxy or represents allyloxy, or representsmethylamino, ethylamino, n- or i-propylamino, n-, i-, s- ort-butylamino, dimethylamino or diethylamino, or represents in each caseoptionally fluoro-, chloro-, bromo-, methyl- or ethyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or representsin each case optionally fluoro-, chloro-, bromo-, cyano-, methyl-,trifluoromethyl- or methoxy-substituted benzyl or phenyl,

R² represents in each case optionally fluoro- and/or chloro-, methyl-and/or ethyl-substituted oxetanyl, thietanyl, furyl, tetrahydrofuryl,thienyl, tetrahydrothienyl, oxetanylmethyl, thietanylmethyl,furylmethyl, tetrahydrofurylmethyl, thienylmethyl ortetrahydrothienylmethyl, and

R³ represents the radical ##STR15## in which R⁴ represents fluoro,chloro, bromo, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy,ethoxy, n- or i-propoxy, n- or i-butoxy, difluoromethoxy,trifluoromethoxy, 2-chloro-ethoxy, 2,2,2-trifluoro-ethoxy,1,1,2,2-tetrafluoro-ethoxy, 1,1,2,2,2-pentafluoro-ethoxy,2-methoxy-ethoxy, methylthio, ethylthio, n- or i-propylthio, n- ori-butylthio, 2-fluoro-ethylthio, allyloxy, propargyloxy,methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl,dimethylaminosuiphonyl, diethylaminosulphonyl,N-methoxy-N-methylaminosulphonyl, phenyl, phenoxy, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, and

R⁵ represents hydrogen, fluoro, chloro, bromo, methyl, ethyl, n- ori-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy,difluoromethoxy, trifluoromethoxy, methylthio or ethylthio;

and also

R³ represents the radical ##STR16## in which R¹⁰ represents hydrogen,

R¹¹ represents fluoro, chloro, bromo, methyl, methoxy, difluoromethoxy,trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl,methylsulphonyl or dimethylaminosulphonyl, and

R¹² represents hydrogen;

and also

R³ represents the radical ##STR17## in which R represents methyl, ethyl,n- or i-propyl, or

R³ represents the radical ##STR18## in which R²⁴ represents methyl,ethyl, n- or i-propyl, phenyl or pyridyl,

R²⁵ represents hydrogen, fluoro, chloro or bromo,

R²⁶ represents fluoro, chloro, bromo, methoxycarbonyl or ethoxycarbonyl.

The radical definitions listed above, given generally or in ranges ofpreference, apply not only to the end products of the formula (I) butalso, correspondingly, to the starting materials and/or intermediatesrequired in each case for preparation. These radical definitions can becombined as desired with one another, thus including combinationsbetween the stated ranges of preferred compounds.

The hydrocarbon radicals mentioned in the radical definitions, such asalkyl, alkenyl or alkinyl, alone or in combination with heteroatoms suchas in alkoxy, alkylthio or alkylamino, are straight-chain or branchedeven if this is not expressly indicated.

Halogen represents generally fluoro, chloro, bromo or iodo, preferablyfluoro, chloro, or bromo, and especially fluoro or chloro.

Using, for example, 2-trifluoromethoxy-phenylsulphonyl isocyanate and4-phenyl-5-(oxetan-3-yl-oxy)-2,4-dihydro-3H-1,2,4-triazol-3-one asstarting materials, the course of reaction in the process (a) accordingto the invention can be illustrated by the following equation: ##STR19##

Using, for example, 2-ethylthio-benzenesulphonamide and2-chlorocarbonyl-4-cyclohexyl-5-(thietan-3-yl-oxy)-2,4-dihydro-3H-1,2,4-triazol-3-oneas starting materials, the course of reaction in the process (b)according to the invention can be illustrated by the following equation:##STR20##

Using, for example N-methoxycarbonyl-2-methoxy-benzenesulphonamide and5-(tetrahydro-2-furyl-methoxy)-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-oneas starting materials, the course of reaction in the process (c)according to the invention can be illustrated by the following equation:##STR21##

Using, for example, 2-chloro-6-methyl-benzenesulphonyl chloride,4-allyl-5-(tetrahydrothienyl-3-oxy)-2,4-dihydro-3H-1,2,4-triazol-3-oneand sodium cyanate as starting materials, the course of reaction in theprocess (d) according to the invention can be illustrated by thefollowing equation: ##STR22##

A general definition of the triazolin(thi)ones to be used as startingmaterials in the processes (a), (c) and (d) according to the inventionfor the preparation of compounds of the formula (I) is given by theformula (II).

In the formula (II), Q¹, R¹ and R² preferably or in particular havethose meanings which have already been indicated above, in connectionwith the description of the compounds of the formula (I) according tothe invention, as being preferable or particularly preferable for Q¹, R¹and R².

The triazolin(thi)ones of the general formula (II) have not yet beendisclosed in the literature; as novel substances, they are also part ofthe present application.

The novel triazolin(thi)ones of the formula (II) are obtained if(thio)carbazinic esters of the general formula (IX) ##STR23## in whichQ¹ has the meaning given above and

R²⁷ represents optionally substituted alkyl (preferably methyl, ethyl,methoxyethyl or ethoxyethyl) or represents phenyl

are reacted with alkyliminocarbonic acid diesters of the general formula(X) ##STR24## in which R¹ and R² have the meanings given above and

G represents alkyl (preferably methyl or ethyl) or has the same meaningas R²,

optionally in the presence of a diluent, for example methanol, andoptionally in the presence of a reaction auxiliary, for example pivalicacid, at temperatures between 0° C. and 100° C., and the compoundsformed in this reaction, of the general formula (XI) ##STR25## in whichQ¹, R¹, R² and R²⁷ have the meanings given above

are subjected--optionally after intermediate isolation--to cyclizingcondensation, optionally in the presence of a diluent, for examplemethanol, and optionally in the presence of a reaction auxiliary, forexample sodium methylate, at temperatures between 20° C. and 150° C.(cf. the preparation examples).

A general definition of the sulphonyl iso(thio)cyanates also to be usedas starting materials in the process (a) according to the invention forthe preparation of compounds of the formula (I) is given by the formula(III).

In the formula (III), Q² and R³ preferably or in particular have thosemeanings which have already been indicated above, in connection with thedescription of the compounds of the formula (I) according to theinvention, as being preferable or particularly preferable for Q² and R³.

The starting materials of the formula (III) are known and/or can beprepared by methods known per se (cf. U.S. Pat. Nos. 4,127,405,4,169,719, 4,371,391, EP A 7 687, EP-A 13 480, EP-A 21 641, EP-A 23 141,EP-A 23 422, EP-A 30 139, EP-A 35 893, EP-A 44 808, EP-A 44 809, EP-A 48143, EP-A 51 466, EP-A 64 322, EP-A 70 041, EP-A 173 312).

A general definition of the triazolin(thi)one derivatives to be used asstarting materials in the process (b) according to the invention for thepreparation of the compounds of the general formula (I) is given by theformula (IV). In the formula (IV), Q¹, Q², R¹ and R² preferably or inparticular have those meanings which have already been indicated above,in connection with the description of the compounds of the formula (I),as being preferable or particularly preferable for Q¹, Q², R¹ and R² ; Zpreferably represents fluoro, chloro, bromo, methoxy, ethoxy, benzyloxy,phenoxy, halogeno- or nitro-phenoxy, in particular methoxy, phenoxy or4-nitro-phenoxy.

The starting materials of the formula (IV) have not yet been disclosedin the literature; as novel substances, they are likewise part of thepresent application.

The novel compounds of the formula (IV) are obtained iftriazolin(thi)ones of the general formula (II) ##STR26## in which Q¹, R¹and R² have the meanings given above

are reacted with carbonic acid derivatives of the general formula (XII)

    Z--CQ.sup.2 --Z.sup.1                                      (XII)

in which

Q² and Z have the meanings given above and

Z¹ represents halogen (especially chloro), alkoxy (especially methoxy),aralkoxy (especially benzyloxy) or aryloxy (especially phenoxy),

optionally in the presence of an acid acceptor, for example sodiumhydride or potassium hydride, sodium hydroxide or potassium hydroxide,sodium t-butylate or potasssium t-butylate, and optionally in thepresence of a diluent, for example tetrahydrofuran or dimethoxyethane,or in a two-phase system comprising water and an organic solvent, forexample methylene chloride or chloroform, at temperatures between 0° C.and 100° C.

A general definition of the sulphonamides also to be used as startingmaterials in the process (b) according to the invention for thepreparation of the compounds of the general formula (I) is given by theformula (V). In the formula (V), R³ preferably or in particular has thatmeaning which has already been indicated above, in connection with thedescription of the compounds of the formula (I), as being preferable orparticularly preferable for R³.

The starting materials of the formula (V) are known and/or can beprepared by methods known per se (cf. U.S. Pat. Nos. 4,127,405,4,169,719, 4,371,391, EP-A 7 687, EP-A 13 480, EP-A 21 641, EP-A 23 141,EP-A 23 422, EP-A 30 139, EP-A 35 893, EP-A 44 808, EP-A 44 809, EP-A 48143, EP-A 51 466, EP-A 64 322, EP-A 70 041, EP-A 173 312).

A general definition of the sulphonamide derivatives to be used asstarting materials in the process (c) according to the invention for thepreparation of the compounds of the formula (I) is given by the formula(VI). In the formula (VI), Q² and R³ preferably or in particular havethose meanings which have already been indicated above, in connectionwith the description of the compounds of the formula (I), as beingpreferable or particularly preferable for Q² and R³ ; Z preferablyrepresents fluoro, chloro, bromo, methoxy, ethoxy, benzyloxy, orphenoxy, especially methoxy or phenoxy.

The starting materials of the formula (VI) are known and/or can beprepared by methods known per se.

A general definition of the sulphonyl halides to be used as startingmaterials in the process (d) according to the invention for thepreparation of the compounds of the formula (I) is given by the formula(VII). In the formula (VII), R³ preferably or in particular has thatmeaning which has already been indicated above, in connection with thedescription of the compounds of the formula (I), as being preferable orparticularly preferable for R³ ; X preferably represents fluoro, chloroor bromo, especially chloro.

The starting materials of the formula (VII) are known and/or can beprepared by methods known per se.

The processes (a), (b), (c) and (d) according to the invention for thepreparation of the novel compounds of the formula (I) are preferablycarried out using diluents. Suitable diluents in this context arevirtually all inert organic solvents. These include, preferably,aliphatic and aromatic, optionally halogenated hydrocarbons such aspentane, hexane, heptane, cyclohexane, petroleum ether, benzine,ligroin, benzene, toluene, xylene, methylene chloride, ethylenechloride, chloroform, tetrachloromethane, chlorobenzene ando-dichlorobenzene; ethers such as diethyl ether and dibutyl ether,glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran anddioxane; ketones such as acetone, methyl ethyl ketone, methyl isopropylketone and methyl isobutyl ketone; esters such as methyl acetate andethyl acetate; nitriles, for example acetonitrile and propionitrile;amides, for example dimethylformamide, dimethylacetamide andN-methyl-pyrrolidone, and also dimethyl sulphoxide, tetramethylenesulphone and hexamethylphosphoric triamide.

As reaction auxiliaries and/or as acid acceptors, it is possible in theprocesses (a), (b), (c) and (d) according to the invention to employ allacid-binding agents which can customarily be used for such reactions.Suitable examples are preferably alkali metal hydroxides such as sodiumhydroxide and potassium hydroxide, alkaline earth metal hydroxides, forexample calcium hydroxide, alkali metal carbonates and alkali metalalcoholates, such as sodium carbonate and potassium carbonate, sodiumtert-butylate and potassium tert-butylate, and also basic nitrogencompounds, such as trimethylamine, triethylamine, tripropylamine,tributylamine, diisobutylamine, dicyclohexylamine,ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzylamine,N,N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-,2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN),1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) and1,4-diazabicyclo-[2.2.2]-octane (DABCO).

The reaction temperatures in the processes (a), (b), (c) and (d)according to the invention can be varied within a relatively largerange. The processes are in general carried out at temperatures between-20° C. and +100° C., preferably at temperatures between 0° C. and +80°C.

The processes (a), (b), (c) and (d) according to the invention are ingeneral carried out under atmospheric pressure. However, it is alsopossible to operate under increased or reduced pressure.

For carrying out the processes (a), (b), (c) and (d) according to theinvention, the starting materials required in each case are in generalemployed in approximately equimolar quantities. However, it is alsopossible to use one of the components employed in each case in arelatively large excess. The reactions are in general carried out in asuitable diluent in the presence of an acid acceptor, and the reactionmixture is stirred for a number of hours at the particular temperaturerequired. Working up in the case of the processes (a), (b), (c) and (d)according to the invention takes place in each case by customary methods(cf. the preparation examples).

From the compounds of the general formula (I) according to the inventionit is possible, if desired, to prepare salts. Such salts are obtained ina simple manner by customary methods of salt formation, for example bydissolving or dispersing a compound of the formula (I) in an appropriatesolvent, for example methylene chloride, acetone, tert-butyl methylether or toluene, and adding an appropriate base. The salts canthen--optionally after prolonged stirring--be isolated by concentrationor filtration with suction.

The active compounds according to the invention can be used asdefoliants, desiccants, agents for destroying broad-leaved plants and,especially, as weed-killers. By weeds, in the broadest sense, there areto be understood all plants which grow in locations where they are notwanted. Whether the substances according to the invention act as totalor selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria,Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio,Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum,Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala,Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis,Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium. However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

The compounds are suitable, depending on the concentration, for thetotal combating of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for combating weeds in perennialcultures, for example afforestations, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, inlawns, turf and pasture-land, and for the selective combating of weedsin annual cultures.

The compounds of the formula (I) according to the invention areparticularly suitable for the selective combating of monocotyledon anddicotyledon weeds in monocotyledon and dicotyledon crops, bothpre-emergence and post-emergence.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surface-active agents, thatis emulsifying agents and/or dispersing agents and/or foam-formingagents.

In the case of the use of water as an extender, organic solvents can,for example, also be used as auxiliary solvents. As liquid solvents,there are suitable in the main: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol as well as their ethers and esters, ketones, suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, as well as water.

As solid carriers there are suitable: for example ammonium salts andground natural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silica, alumina and silicates, assolid carriers for granules there are suitable: for example crushed andfractionated natural minerals such as calcite, marble, pumice, sepioliteand dolomite, as well as synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,maize cobs and tobacco stalks; as emulsifying and/or foamforming agentsthere are suitable: for example nonionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as well as albumen hydrolysis products; asdispersing agents there are suitable: for example lignin-sulphite wasteliquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Further additives can bemineral and vegetable oils.

It is possible to use colourants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyes, such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and tracenutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

For combating weeds, the active compounds according to the invention, assuch or in the form of their formulations, can also be used as mixtureswith known herbicides, finished formulations or tank mixes beingpossible.

Suitable co-components for the mixtures are known herbicides, forexample anilides, for example diflufenican and propanil; arylcarboxylicacids, for example dichloropicolinic acid, dicamba and picloram;aryloxyalkanoic acids, for example 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr,MCPA, MCPP and triclopyr; aryloxy-phenoxy alkanoic esters for examplediclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl andquizalofop-ethyl; azinones, for example chloridazone and norflurazone;carbamates, for example chlorpropham, desmedipham, phenmedipham andpropham; chloroacetanilides, for example alachlor, acetochlor,butachlor, metazachlor, metolachlor, pretilachlor and propachlor;dinitroanilines, for example oryzalin, pendimethalin and trifluralin;diphenyl ethers, for example acifluorfen, bifenox, fluoroglycofen,fomesafen, halosafen, lactofen and oxyfluorfen; ureas, for examplechlorotoluron, diuron, fluometuron, isoproturon, linuron andmethabenzthiazuron; hydroxylamines, for example alloxydim, clethodim,cycloxydim, sethoxydim and tralkoxydim; imidazolinones, for exampleimazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles, forexample bromoxynil, dichlobenil and ioxynil; oxyacetamides, for examplemefenacet; sulphonyl ureas, for example amidosulfuron,bensulfuron-methyl, chlorimuronethyl, chlorsulfuron, cinosulfuron,metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl,thifensulfuron-methyl, triasulfuron and tribenuron-methyl;thiolcarbamates, for example butylate, cycloate, diallate, EPTC,esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines,for example atrazine, cyanazine, simazine, simetryne, terbutryne andterbutylazine; triazinones, for example hexazinone, metamitron andmetribuzin; others, for example aminotriazole, benfuresate, bentazone,cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr,ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben,pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellants, plant nutrientsand agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 1 g and 10 kg of active compound perhectare of soil surface, preferably between 5 g and 2 kg per ha.

The preparation and use of the active compounds according to theinvention can be seen from the following examples.

PREPARATION EXAMPLES Example 1 ##STR27## (Process (a))

A mixture of 1.3 g (7 mmol) of4-methyl-5-(3-tetrahydrofuryi-oxy)-2,4-dihydro-3H-1,2,4-triazol-3-one,2.24 g (8.4 mmol) of 2-trifluoromethoxy-phenylsulphonyl isocyanate and60 ml of acetonitrile is stirred at about 20° C. for 16 hours. It isthen concentrated under a water pump vacuum, the residue is stirred withisopropanol/petroleum ether (volume about 3/7) and the crystallineproduct obtained in this procedure is isolated by filtration withsuction.

3.0 g (94% of theory) of4-methyl-5-(3-tetrahydrofuryl-oxy)-2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneare obtained of melting point 184° C.

Example 2 ##STR28## (Process (b))

2.5 g (10 mmol) of 2-bromo-benzolsulphonamide are dissolved in 40 mlacetonitrile, and 3.2 g (10 mmol) of4-methyl-2-phenoxycarbonyl-5-(3-tetrahydrofuryl-oxy)-2,4-dihydro-3H-1,2,4-triazol-3-oneand 1.6 g (10 mmol) of diazabicycloundecene (DBU) are added withstrirring. The mixture is stirred at 20° C. for 12 hours and thenconcentrated under a water pump vacuum. The residue is taken up inmethylene chloride and the mixture is washed with 10% strengthhydrochloric acid, dried over sodium sulphate and filtered. The filtrateis concentrated under a water pump vacuum, the residue is digested withisopropanol/petroleum ether (1/5) and the crystalline product obtainedis isolated by filtration with suction.

3.5 g (78% of theory) of2-(2-bromo-phenylsulphonyl-aminocarbonyl)-4-methyl-5-(3-tetrahydrofuryl-oxy)-2,4-dihydro-3H-1,2,4-triazol-3-oneare obtained of melting point 191° C.

In analogy to Example 1 or 2 and in accordance with the generaldescription of the preparation processes according to the invention itis also possible, for example, to prepare the compounds of the formula(I) which are listed in Table I below. ##STR29##

                                      TABLE 1                                     __________________________________________________________________________    Examples of the compounds of the formula (I)                                                                                   Melting                      Ex. No.                                                                            Q.sup.1                                                                          Q.sup.2                                                                          R.sup.1  R.sup.2       R.sup.3        point (° C.)          __________________________________________________________________________    3    O  O  CH.sub.3                                                                                              ##STR30##     185                          4    O  O  CH.sub.3                                                                                ##STR31##                                                                                   ##STR32##     178                          5    O  O  CH.sub.3                                                                                ##STR33##                                                                                   ##STR34##     187                          6    O  O  CH.sub.3                                                                                ##STR35##                                                                                   ##STR36##     185                          7    O  O  CH.sub.3                                                                                ##STR37##                                                                                   ##STR38##     167                          8    O  O  CH.sub.3                                                                                ##STR39##                                                                                   ##STR40##     143                          9    O  O  CH.sub.3                                                                                ##STR41##                                                                                   ##STR42##     181                          10   O  O                                                                                 ##STR43##                                                                              ##STR44##                                                                                   ##STR45##     200                          11   O  O  CH.sub.3                                                                                ##STR46##                                                                                   ##STR47##                                  12   O  O  CH.sub.3                                                                                ##STR48##                                                                                   ##STR49##                                  13   O  O  CH.sub.3                                                                                ##STR50##                                                                                   ##STR51##                                  14   O  O  CH.sub.3                                                                                ##STR52##                                                                                   ##STR53##                                  15   O  O  CH.sub.3                                                                                ##STR54##                                                                                   ##STR55##                                  16   O  O  CH.sub.3                                                                                ##STR56##                                                                                   ##STR57##                                  17   O  O  CH.sub.3                                                                                ##STR58##                                                                                   ##STR59##                                  18   O  O  CH.sub.3                                                                                ##STR60##                                                                                   ##STR61##                                  19   O  O  CH.sub.3                                                                                ##STR62##                                                                                   ##STR63##                                  20   O  O  CH.sub.3                                                                                ##STR64##                                                                                   ##STR65##                                  21   O  O  CH.sub.3                                                                                ##STR66##                                                                                   ##STR67##                                  22   O  O  CH.sub.3                                                                                ##STR68##                                                                                   ##STR69##                                  23   O  O  CH.sub.3                                                                                ##STR70##                                                                                   ##STR71##                                  24   O  O  CH.sub.3                                                                                ##STR72##                                                                                   ##STR73##                                  25   O  O  CH.sub.3                                                                                ##STR74##                                                                                   ##STR75##                                  26   O  O  CH.sub.3                                                                                ##STR76##                                                                                   ##STR77##                                  27   O  O  CH.sub.3                                                                                ##STR78##                                                                                   ##STR79##                                  28   O  O  CH.sub.3                                                                                ##STR80##                                                                                   ##STR81##                                  29   O  O  CH.sub.3                                                                                ##STR82##                                                                                   ##STR83##                                  30   O  O                                                                                 ##STR84##                                                                              ##STR85##                                                                                   ##STR86##                                  31   O  O                                                                                 ##STR87##                                                                              ##STR88##                                                                                   ##STR89##                                  32   O  O                                                                                 ##STR90##                                                                              ##STR91##                                                                                   ##STR92##                                  33   O  O                                                                                 ##STR93##                                                                              ##STR94##                                                                                   ##STR95##                                  34   O  O                                                                                 ##STR96##                                                                              ##STR97##                                                                                   ##STR98##     103                          35   O  O                                                                                 ##STR99##                                                                              ##STR100##                                                                                  ##STR101##                                 36   O  O                                                                                 ##STR102##                                                                             ##STR103##                                                                                  ##STR104##                                 37   O  O                                                                                 ##STR105##                                                                             ##STR106##                                                                                  ##STR107##                                 38   O  O                                                                                 ##STR108##                                                                             ##STR109##                                                                                  ##STR110##                                 39   O  O                                                                                 ##STR111##                                                                             ##STR112##                                                                                  ##STR113##                                 40   O  O                                                                                 ##STR114##                                                                             ##STR115##                                                                                  ##STR116##                                 41   O  O                                                                                 ##STR117##                                                                             ##STR118##                                                                                  ##STR119##                                 42   O  O                                                                                 ##STR120##                                                                             ##STR121##                                                                                  ##STR122##                                 43   O  O                                                                                 ##STR123##                                                                             ##STR124##                                                                                  ##STR125##                                 44   O  O                                                                                 ##STR126##                                                                             ##STR127##                                                                                  ##STR128##                                 45   O  O                                                                                 ##STR129##                                                                             ##STR130##                                                                                  ##STR131##                                 46   O  O                                                                                 ##STR132##                                                                             ##STR133##                                                                                  ##STR134##                                 47   O  O                                                                                 ##STR135##                                                                             ##STR136##                                                                                  ##STR137##                                 48   O  O                                                                                 ##STR138##                                                                             ##STR139##                                                                                  ##STR140##                                 49   O  O                                                                                 ##STR141##                                                                             ##STR142##                                                                                  ##STR143##                                 50   O  O                                                                                 ##STR144##                                                                             ##STR145##                                                                                  ##STR146##                                 51   O  O                                                                                 ##STR147##                                                                             ##STR148##                                                                                  ##STR149##                                 52   O  O                                                                                 ##STR150##                                                                             ##STR151##                                                                                  ##STR152##                                 53   O  O                                                                                 ##STR153##                                                                             ##STR154##                                                                                  ##STR155##                                 54   O  O                                                                                 ##STR156##                                                                             ##STR157##                                                                                  ##STR158##                                 55   O  O                                                                                 ##STR159##                                                                             ##STR160##                                                                                  ##STR161##                                 56   O  O                                                                                 ##STR162##                                                                             ##STR163##                                                                                  ##STR164##                                 57   O  O                                                                                 ##STR165##                                                                             ##STR166##                                                                                  ##STR167##                                 58   O  O                                                                                 ##STR168##                                                                             ##STR169##                                                                                  ##STR170##                                 59   O  O                                                                                 ##STR171##                                                                             ##STR172##                                                                                  ##STR173##                                 60   O  O                                                                                 ##STR174##                                                                             ##STR175##                                                                                  ##STR176##                                 61   O  O                                                                                 ##STR177##                                                                             ##STR178##                                                                                  ##STR179##                                 62   O  O                                                                                 ##STR180##                                                                             ##STR181##                                                                                  ##STR182##                                 63   O  O                                                                                 ##STR183##                                                                             ##STR184##                                                                                  ##STR185##                                 64   O  O                                                                                 ##STR186##                                                                             ##STR187##                                                                                  ##STR188##                                 65   O  O                                                                                 ##STR189##                                                                             ##STR190##                                                                                  ##STR191##                                 66   O  O                                                                                 ##STR192##                                                                             ##STR193##                                                                                  ##STR194##                                 67   O  O                                                                                 ##STR195##                                                                             ##STR196##                                                                                  ##STR197##                                 68   O  O                                                                                 ##STR198##                                                                             ##STR199##                                                                                  ##STR200##                                 69   O  O                                                                                 ##STR201##                                                                             ##STR202##                                                                                  ##STR203##                                 70   O  O                                                                                 ##STR204##                                                                             ##STR205##                                                                                  ##STR206##                                 71   O  O                                                                                 ##STR207##                                                                             ##STR208##                                                                                  ##STR209##                                 72   O  O                                                                                 ##STR210##                                                                             ##STR211##                                                                                  ##STR212##                                 73   O  O                                                                                 ##STR213##                                                                             ##STR214##                                                                                  ##STR215##                                 74   O  O                                                                                 ##STR216##                                                                             ##STR217##                                                                                  ##STR218##                                 75   O  O                                                                                 ##STR219##                                                                             ##STR220##                                                                                  ##STR221##                                 76   O  O                                                                                 ##STR222##                                                                             ##STR223##                                                                                  ##STR224##                                 77   O  O                                                                                 ##STR225##                                                                             ##STR226##                                                                                  ##STR227##                                 78   O  O                                                                                 ##STR228##                                                                             ##STR229##                                                                                  ##STR230##                                 79   O  O                                                                                 ##STR231##                                                                             ##STR232##                                                                                  ##STR233##                                 80   O  O                                                                                 ##STR234##                                                                             ##STR235##                                                                                  ##STR236##                                 81   O  O                                                                                 ##STR237##                                                                             ##STR238##                                                                                  ##STR239##                                 82   O  O                                                                                 ##STR240##                                                                             ##STR241##                                                                                  ##STR242##                                 83   O  O                                                                                 ##STR243##                                                                             ##STR244##                                                                                  ##STR245##                                 84   O  O                                                                                 ##STR246##                                                                             ##STR247##                                                                                  ##STR248##                                 85   O  O                                                                                 ##STR249##                                                                             ##STR250##                                                                                  ##STR251##                                 86   O  O                                                                                 ##STR252##                                                                             ##STR253##                                                                                  ##STR254##                                 87   O  O  OCH.sub.3                                                                               ##STR255##                                                                                  ##STR256##                                 88   O  O  OCH.sub.3                                                                               ##STR257##                                                                                  ##STR258##                                 89   O  O  OCH.sub.3                                                                               ##STR259##                                                                                  ##STR260##                                 90   O  O  OCH.sub.3                                                                               ##STR261##                                                                                  ##STR262##                                 91   O  O  OCH.sub.3                                                                               ##STR263##                                                                                  ##STR264##                                 92   O  O  OCH.sub.3                                                                               ##STR265##                                                                                  ##STR266##                                 93   O  O  OCH.sub.3                                                                               ##STR267##                                                                                  ##STR268##                                 94   O  O  OCH.sub.3                                                                               ##STR269##                                                                                  ##STR270##                                 95   O  O  OCH.sub.3                                                                               ##STR271##                                                                                  ##STR272##                                 96   O  O  OCH.sub.3                                                                               ##STR273##                                                                                  ##STR274##                                 97   O  O  OCH.sub.3                                                                               ##STR275##                                                                                  ##STR276##                                 98   O  O  OCH.sub.3                                                                               ##STR277##                                                                                  ##STR278##                                 99   O  O  OCH.sub.3                                                                               ##STR279##                                                                                  ##STR280##                                 100  O  O  OCH.sub.3                                                                               ##STR281##                                                                                  ##STR282##                                 101  O  O  OCH.sub.3                                                                               ##STR283##                                                                                  ##STR284##                                 102  O  O  OCH.sub.3                                                                               ##STR285##                                                                                  ##STR286##                                 103  O  O  OCH.sub.3                                                                               ##STR287##                                                                                  ##STR288##                                 104  O  O  OCH.sub.3                                                                               ##STR289##                                                                                  ##STR290##                                 105  O  O  OCH.sub.3                                                                               ##STR291##                                                                                  ##STR292##                                 106  O  O  OC.sub.2 H.sub.5                                                                        ##STR293##                                                                                  ##STR294##                                 107  O  O  OC.sub.2 H.sub.5                                                                        ##STR295##                                                                                  ##STR296##                                 108  O  O  OC.sub.2 H.sub.5                                                                        ##STR297##                                                                                  ##STR298##                                 109  O  O  OC.sub.2 H.sub.5                                                                        ##STR299##                                                                                  ##STR300##                                 110  O  O  OC.sub.2 H.sub.5                                                                        ##STR301##                                                                                  ##STR302##                                 111  O  O  OC.sub.2 H.sub.5                                                                        ##STR303##                                                                                  ##STR304##                                 112  O  O  OC.sub.2 H.sub.5                                                                        ##STR305##                                                                                  ##STR306##                                 113  O  O  OCH.sub.3                                                                               ##STR307##                                                                                  ##STR308##                                 114  O  O  OC.sub.2 H.sub.5                                                                        ##STR309##                                                                                  ##STR310##                                 115  O  O  OC.sub.2 H.sub.5                                                                        ##STR311##                                                                                  ##STR312##                                 116  O  O  OC.sub.2 H.sub.5                                                                        ##STR313##                                                                                  ##STR314##                                 117  O  O  OC.sub.2 H.sub.5                                                                        ##STR315##                                                                                  ##STR316##                                 118  O  O  OC.sub.2 H.sub.5                                                                        ##STR317##                                                                                  ##STR318##                                 119  O  O  OC.sub.2 H.sub.5                                                                        ##STR319##                                                                                  ##STR320##                                 120  O  O  OC.sub.2 H.sub.5                                                                        ##STR321##                                                                                  ##STR322##                                 121  O  O  OCH.sub.3                                                                               ##STR323##                                                                                  ##STR324##                                 122  O  O  OC.sub.2 H.sub.5                                                                        ##STR325##                                                                                  ##STR326##                                 123  O  O  OC.sub.2 H.sub.5                                                                        ##STR327##                                                                                  ##STR328##                                 124  O  O  OC.sub.2 H.sub.5                                                                        ##STR329##                                                                                  ##STR330##                                 __________________________________________________________________________

Starting Materials of the Formula (II):

Example (II-1) ##STR331## Step 1: ##STR332##

233 g (2.65 mol) of 3-hydroxy-tetrahydrofuran are azeotropicallydewatered in 750 ml toluene under a water pump vacuum at 50 mbar. Then,with ice cooling, 18 g (0.60 mol) of sodium hydride (80% pure) are addedover the course of about 20 minutes. After 30 minutes, 176 g (2.41 mol)of methyl isothiocyanate are added dropwise over the course of about 30minutes at 50° C., with ice cooling. The reaction mixture is thenstirred at 50° C. for about 2 hours more. It is subsequently neutralizedwith 71.2 g of 30.7% strength hydrochloric acid (0.60 mol of HCl), withice cooling, and finally is azeotropically dewatered at 100 mbar andfiltered, and the filtrate is concentrated to about 500 g.

Step 2: ##STR333##

782 g (2.65 mol) of dibutyltin dimethoxide are initially introduced at40° C. under an oil pump vacuum, and the product solution obtained instep 1 is added dropwise over the course of about 30 minutes. Duringthis addition, methanol is distilled off and the temperature is raisedto about 80° C. Subsequently, the air is replaced by nitrogen and thereaction mixture is stirred at 100° C. for 16 hours. It is thenrectified under an oil pump vacuum. Following the distillation of aninitial fraction of 43 g, 290 ml of main fraction are obtained (at 1mbar/60° C.), which according to analysis by gas chromatography consistof 203.5 g (1.28 mol) of methylimino-carbonic acid O-methyl esterO-(3-tetrahydrofuryl) ester and 75.2 g (0.35 mol) ofmethylimino-carbonic acid O,O-bis(3-tetrahydrofuryl) ester.

Step 3: ##STR334##

261 g (1.63 mol) of 2-ethoxyethyl carbazinate are initially introducedat 0° C. and the product mixture from step 2, which has been cooled to0° C., is added all at once. Then 1.66 g portions of pivalic acid areadded at intervals of about 20 minutes and the mixture is stirred at 20°C. for 16 hours and then at 45° C. for 30 minutes more. Following theaddition of 299 g of 30% strength methanol sodium methylate solution(1.66 mol sodium methylate), the mixture is stirred at 55° C. for afurther 3 hours. After it has cooled, the reaction mixture isneutralized with 197 g of 30.7% strength hydrochloric acid (1.66 mol ofHCl), with ice cooling, and then concentrated under a water pump vacuum.The residue is recrystallized from 750 ml of toluene, to give 209 g of aproduct mixture which, according to analysis by gas chromatography,consists to the extent of 51% of4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one and to the extentof 43% of4-methyl-5-(3-tetrahydrofuryl-oxy)-2,4-dihydro-3H-1,2,4-triazol-3-one.The product mixture is recrystallized from 400 ml of water, giving 50 gof 4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one as acrystalline product. The mother liquor is concentrated by evaporationand the residue is recrystallized from 400 ml of toluene. Renewedrecrystallization of the product from methanol gives 83 g (0.45 mol) of4-methyl-5-(3-tetrahydrofuryl-oxy)-2,4-dihydro-3H- 1,2,4-triazol-3-oneof melting point 164° C.

In analogy to Example (II-1) it is also possible, for example, toprepare the compounds of the formula (II) which are listed in Table 2below. ##STR335##

                  TABLE 2                                                         ______________________________________                                        Examples of the compounds of the formula (II)                                                                     Melting                                   Ex. No.                                                                             Q.sup.1                                                                             R.sup.1     R.sup.2     point (° C.)                       ______________________________________                                        II-2  O     CH.sub.3                                                          II-3  O     CH.sub.3                                                                                   ##STR336##                                           II-4  O     CH.sub.3                                                                                   ##STR337##                                           II-5  O     CH.sub.3                                                                                   ##STR338##                                           II-6  O     CH.sub.3                                                                                   ##STR339##                                           II-7  O                                                                                    ##STR340##                                                                                ##STR341##                                           II-8  O                                                                                    ##STR342##                                                                                ##STR343##                                           II-9  O                                                                                    ##STR344##                                                                                ##STR345##                                           II-10 O                                                                                    ##STR346##                                                                                ##STR347##                                           II-11 O                                                                                    ##STR348##                                                                                ##STR349##                                           II-12 O                                                                                    ##STR350##                                                                                ##STR351##                                           II-13 O                                                                                    ##STR352##                                                                                ##STR353##                                           II-14 O                                                                                    ##STR354##                                                                                ##STR355##                                           II-15 O                                                                                    ##STR356##                                                                                ##STR357##                                           II-16 O                                                                                    ##STR358##                                                                                ##STR359##                                           II-17 O                                                                                    ##STR360##                                                                                ##STR361##                                           II-18 O                                                                                    ##STR362##                                                                                ##STR363##                                           II-19 O                                                                                    ##STR364##                                                                                ##STR365##                                           II-20 O                                                                                    ##STR366##                                                                                ##STR367##                                           II-21 O                                                                                    ##STR368##                                                                                ##STR369##                                           II-22 O     OCH.sub.3                                                                                  ##STR370##                                           II-23 O     OCH.sub.3                                                                                  ##STR371##                                           II-24 O     OCH.sub.3                                                                                  ##STR372##                                           II-25 O     OCH.sub.3                                                                                  ##STR373##                                           II-26 O     OCH.sub.3                                                                                  ##STR374##                                           II-27 O     OC.sub.2 H.sub.5                                                                           ##STR375##                                           II-28 O     OC.sub.2 H.sub.5                                                                           ##STR376##                                           II-29 O     OC.sub.2 H.sub.5                                                                           ##STR377##                                           II-30 O     OC.sub.2 H.sub.5                                                                           ##STR378##                                           II-31 O     OC.sub.2 H.sub.5                                                                           ##STR379##                                           II-32 O     N(CH.sub.3).sub.2                                                                          ##STR380##                                           II-33 O     N(CH.sub.3).sub.2                                                                          ##STR381##                                           II-34 O     N(CH.sub.3).sub.2                                                                          ##STR382##                                           II-35 O     N(CH.sub.3).sub.2                                                                          ##STR383##                                           II-36 O     N(CH.sub.3).sub.2                                                                          ##STR384##                                           ______________________________________                                    

Starting Materials of the Formula (IV):

Example (IV-1) ##STR385##

6.9 g (44 mmol) of phenyl chloroformate are added dropwise with stirringat from 20° C. to 30° C. to a mixture of 7.4 g (40 mmol) of4-methyl-5-(3-tetrahydrofuryloxy)-2,4-dihydro-3H-1,2,4-triazol-3-one,1.8 g (44 mmol) of sodium hydroxide, 0.2 g of tetrabutylammoniumchloride, 50 ml of water and 50 ml of methylene chloride, and thereaction mixture is stirred at 20° C. for 12 hours. The organic phase issubsequently separated off, washed with water, dried over sodiumsulphate and filtered. The filtrate is concentrated under a water pumpvacuum, the residue is digested with petroleum ether, and thecrystalline product obtained in this procedure is isolated by filtrationwith suction.

11.8 g (97% of theory) of4-methyl-2-phenoxycarbonyl-5-(3-tetrahydrofuryloxy)-2,4-dihydro-3H-1,2,4-triazol-3-oneare obtained of melting point 98° C.

In analogy to Example (IV-1) it is also possible, for example, toprepare the compounds of the formula (IV) which are listed in Table 3below. ##STR386##

                                      TABLE 3                                     __________________________________________________________________________    Examples of the compounds of the formula (IV)                                                                     Melting                                   Ex. No.                                                                            Q.sup.1                                                                          Q.sup.2                                                                          R.sup.1  R.sup.2    Z    point (° C.)                       __________________________________________________________________________    IV-2 S  O  CH.sub.3                                                                                          OC.sub.6 H.sub.5                               IV-3 O  O  CH.sub.3                                                                                ##STR387##                                                                              OC.sub.6 H.sub.5                               IV-4 O  O  CH.sub.3                                                                                ##STR388##                                                                              Cl                                             IV-5 S  O  CH.sub.3                                                                                ##STR389##                                                                              OC.sub.6 H.sub.5                               IV-6 S  O  CH.sub.3                                                                                ##STR390##                                                                              Cl                                             IV-7 O  O  CH.sub.3                                                                                ##STR391##                                                                              OC.sub.6 H.sub.5                               IV-8 O  O  CH.sub.3                                                                                ##STR392##                                                                              OC.sub.6 H.sub.5                               IV-9 O  O  CH.sub.3                                                                                ##STR393##                                                                              OC.sub.6 H.sub.5                               IV-10                                                                              S  O                                                                                 ##STR394##                                                                             ##STR395##                                                                              OC.sub.6 H.sub.5                               IV-11                                                                              O  O                                                                                 ##STR396##                                                                             ##STR397##                                                                              OC.sub.6 H.sub.5                               IV-12                                                                              O  O                                                                                 ##STR398##                                                                             ##STR399##                                                                              Cl                                             IV-13                                                                              S  O                                                                                 ##STR400##                                                                             ##STR401##                                                                              OC.sub.6 H.sub.5                               IV-14                                                                              S  O                                                                                 ##STR402##                                                                             ##STR403##                                                                              Cl                                             IV-15                                                                              O  O                                                                                 ##STR404##                                                                             ##STR405##                                                                              OC.sub.6 H.sub.5                               IV-16                                                                              O  O                                                                                 ##STR406##                                                                             ##STR407##                                                                              OC.sub.6 H.sub.5                               IV-17                                                                              O  O                                                                                 ##STR408##                                                                             ##STR409##                                                                              OC.sub.6 H.sub.5                               IV-18                                                                              S  O  C.sub.2 H.sub.5                                                                         ##STR410##                                                                              OC.sub.6 H.sub.5                               IV-19                                                                              O  O  C.sub.2 H.sub.5                                                                         ##STR411##                                                                              OC.sub.6 H.sub.5                               IV-20                                                                              O  O  C.sub.2 H.sub.5                                                                         ##STR412##                                                                              Cl                                             IV-21                                                                              S  O  C.sub.2 H.sub.5                                                                         ##STR413##                                                                              OC.sub.6 H.sub.5                               IV-22                                                                              S  O  C.sub.2 H.sub.5                                                                         ##STR414##                                                                              Cl                                             IV-23                                                                              O  O  C.sub.2 H.sub.5                                                                         ##STR415##                                                                              OC.sub.6 H.sub.5                               IV-24                                                                              O  O  C.sub.2 H.sub.5                                                                         ##STR416##                                                                              OC.sub.6 H.sub.5                               IV-25                                                                              O  O  C.sub.2 H.sub.5                                                                         ##STR417##                                                                              OC.sub.6 H.sub.5                               IV-26                                                                              S  O                                                                                 ##STR418##                                                                             ##STR419##                                                                              OC.sub.6 H.sub.5                               IV-27                                                                              O  O                                                                                 ##STR420##                                                                             ##STR421##                                                                              OC.sub.6 H.sub.5                               IV-28                                                                              O  O                                                                                 ##STR422##                                                                             ##STR423##                                                                              Cl                                             IV-29                                                                              S  O                                                                                 ##STR424##                                                                             ##STR425##                                                                              OC.sub.6 H.sub.5                               IV-30                                                                              S  O                                                                                 ##STR426##                                                                             ##STR427##                                                                              Cl                                             IV-31                                                                              O  O                                                                                 ##STR428##                                                                             ##STR429##                                                                              OC.sub.6 H.sub.5                               IV-32                                                                              O  O                                                                                 ##STR430##                                                                             ##STR431##                                                                              OC.sub.6 H.sub.5                               IV-33                                                                              O  O                                                                                 ##STR432##                                                                             ##STR433##                                                                              OC.sub.6 H.sub.5                               IV-34                                                                              S  O  N(CH.sub.3).sub.2                                                                       ##STR434##                                                                              OC.sub.6 H.sub.5                               IV-35                                                                              O  O  N(CH.sub.3).sub.2                                                                       ##STR435##                                                                              OC.sub.6 H.sub.5                               IV-36                                                                              O  O  N(CH.sub.3).sub.2                                                                       ##STR436##                                                                              Cl                                             IV-37                                                                              S  O  N(CH.sub.3).sub.2                                                                       ##STR437##                                                                              OC.sub.6 H.sub.5                               IV-38                                                                              S  O  N(CH.sub.3).sub.2                                                                       ##STR438##                                                                              Cl                                             IV-39                                                                              O  O  N(CH.sub.3).sub.2                                                                       ##STR439##                                                                              OC.sub.6 H.sub.5                               IV-40                                                                              O  O  N(CH.sub.3).sub.2                                                                       ##STR440##                                                                              OC.sub.6 H.sub.5                               IV-41                                                                              O  O  N(CH.sub.3).sub.2                                                                       ##STR441##                                                                              OC.sub.6 H.sub.5                               IV-42                                                                              S  O  OCH.sub.3                                                                               ##STR442##                                                                              OC.sub.6 H.sub.5                               IV-43                                                                              O  O  OCH.sub.3                                                                               ##STR443##                                                                              OC.sub.6 H.sub.5                               IV-44                                                                              O  O  OCH.sub.3                                                                               ##STR444##                                                                              Cl                                             IV-45                                                                              S  O  OCH.sub.3                                                                               ##STR445##                                                                              OC.sub.6 H.sub.5                               IV-46                                                                              S  O  OCH.sub.3                                                                               ##STR446##                                                                              Cl                                             IV-47                                                                              O  O  OCH.sub.3                                                                               ##STR447##                                                                              OC.sub.6 H.sub.5                               IV-48                                                                              O  O  OCH.sub.3                                                                               ##STR448##                                                                              OC.sub.6 H.sub.5                               IV-49                                                                              O  O  OCH.sub.3                                                                               ##STR449##                                                                              OC.sub.6 H.sub.5                               IV-50                                                                              S  O  OC.sub.2 H.sub.5                                                                        ##STR450##                                                                              OC.sub.6 H.sub.5                               IV-51                                                                              O  O  OC.sub.2 H.sub.5                                                                        ##STR451##                                                                              OC.sub.6 H.sub.5                               IV-52                                                                              O  O  OC.sub.2 H.sub.5                                                                        ##STR452##                                                                              Cl                                             IV-53                                                                              S  O  OC.sub.2 H.sub.5                                                                        ##STR453##                                                                              OC.sub.6 H.sub.5                               IV-54                                                                              S  O  OC.sub.2 H.sub.5                                                                        ##STR454##                                                                              Cl                                             IV-55                                                                              O  O  OC.sub.2 H.sub.5                                                                        ##STR455##                                                                              OC.sub.6 H.sub.5                               IV-56                                                                              O  O  OC.sub.2 H.sub.5                                                                        ##STR456##                                                                              OC.sub.6 H.sub.5                               IV-57                                                                              O  O  OC.sub.2 H.sub.5                                                                        ##STR457##                                                                              OC.sub.6 H.sub.5                               IV-58                                                                              S  O                                                                                 ##STR458##                                                                             ##STR459##                                                                              OC.sub.6 H.sub.5                               IV-59                                                                              O  O                                                                                 ##STR460##                                                                             ##STR461##                                                                              OC.sub.6 H.sub.5                               IV-60                                                                              O  O                                                                                 ##STR462##                                                                             ##STR463##                                                                              Cl                                             IV-61                                                                              S  O                                                                                 ##STR464##                                                                             ##STR465##                                                                              OC.sub.6 H.sub.5                               IV-62                                                                              S  O                                                                                 ##STR466##                                                                             ##STR467##                                                                              Cl                                             IV-63                                                                              O  O                                                                                 ##STR468##                                                                             ##STR469##                                                                              OC.sub.6 H.sub.5                               IV-64                                                                              O  O                                                                                 ##STR470##                                                                             ##STR471##                                                                              OC.sub.6 H.sub.5                               IV-65                                                                              O  O                                                                                 ##STR472##                                                                             ##STR473##                                                                              OC.sub.6 H.sub.5                               __________________________________________________________________________

Use Examples Example A

Pre-emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil and, after about 24hours, the soil is watered with the preparation of the active compound.It is expedient to keep constant the amount of water per unit area. Theconcentration of the active compound in the preparation is of noimportance, only the amount of active compound applied per unit areabeing decisive.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

0%=no action (like untreated control)

100%=total destruction

In this test, the compounds of the formula (I) according to theinvention exhibit a strong action against weeds (see Table A).

Example B

Post-emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is so chosen that the particularamounts of active compound desired are applied in 1,000 l of water/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

0%=no action (like untreated control)

100%=total destruction

In this test, the compounds of the formula (I) according to theinvention exhibit a strong action against weeds (see Table B).

                                      TABLE A                                     __________________________________________________________________________    Pre-emergence test/greenhouse                                                 Active Compound according                                                     to Example No.                                                                             g ai./ha                                                                          Alopecurus                                                                          Bromus                                                                            Cyperus                                                                           Lolium                                                                            Amaranthus                                                                          Cassia                                                                            Chenopodium                                                                          Veronica                  __________________________________________________________________________    (34)         500 100   100 100 100 100   100 100    100                       __________________________________________________________________________     [see Table 1]-                                                           

                  TABLE B                                                         ______________________________________                                        Post-emergence test/greenhouse                                                Active Com-                                                                   pound accord-                                                                 ing to Example                                                                No.      g ai./ha                                                                              Amaranthus                                                                              Solanum                                                                              Stellaria                                                                           Xanthium                              ______________________________________                                        (34)     500     95        95     90    95                                    ______________________________________                                         [See Table 1]-                                                           

We claim:
 1. A compound of the formula (I) ##STR474## wherein Q¹represents oxygen or sulphur,Q² represents oxygen or sulphur, R¹represents hydrogen, hydroxyl, amino or C₁ -C₆ -alkylideneamino, orrepresents optionally fluoro-, chloro-, bromo-, cyano-, C₁ -C₄ -alkoxy-,C₁ -C₄ -alkylcarbonyl- or C₁ -C₄ -alkoxy-cabonyl-substituted C₁ -C₆-alkyl, or represents in each case optionally fluoro-, chloro- and/orbromo-substituted C₂ -C₆ -alkenyl or C₂ -C₆ -alkinyl, or represents C₁-C₆ -alkyloxy or C₃ -C₆ -alkenyloxy, or represents in each caseoptionally fluoro- and/or chloro-substituted C₁ -C₆ -alkylamino, di-(C₁-C₄ -alkyl)-amino or C₁ -C₄ -alkanoylamino, or represents in each caseoptionally fluoro-, chloro-, bromo- and/or C₁ -C₄ -alkyl-substituted C₃-C₆ -cycloalkyl or C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, or represents ineach case optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C₁ -C₄-alkyl-, trifluoromethyl-, C₁ -C₄ -alkoxy- and/or C₁ -C₄-alkoxy-carbonyl-substituted phenyl or phenyl-C₁ -C₄ -alkyl, R²represents in each case optionally halogeno- and/or C₁ -C₄ -alkylsubstituted oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl,tetrahydrothienyl, oxetanyl-C₁ -C₄ -alkyl, thietanyl-C₁ -C₄ -alkyl,furyl-C₁ -C₄ -alkyl, tetrahydrofuryl-C₁ -C₄ -alkyl, thienyl-C₁ -C₄-alkyl, tetrahydrothienyl-C₁ -C₄ -alkyl, and R³ represents the group##STR475## in which R⁴ and R⁵ are identical or different and representhydrogen, fluoro, chloro, bromo, iodo, nitro or C₁ -C₆ -alkyl (which isoptionally substituted by fluoro, chloro, bromo, cyano, carboxyl, C₁ -C₄-alkoxycarbonyl, C₁ -C₄ -alkylamino-carbonyl, di-(C₁ -C₄-alkyl)-amino-carbonyl, hydroxyl, C₁ -C₄ -alkoxy, formyloxy, C₁ -C₄-alkyl-carbonyloxy, C₁ -C₄ -alkylamino-carbonyloxy, C₁ -C₄ -alkylthio,C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, di-(C₁ -C₄-alkyl)-amino-sulphonyl, C₃ -C₆ -cycloalkyl or phenyl), or represent C₂-C₆ -alkenyl (which is optionally substituted by fluoro, chloro, bromo,cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), or represent C₂ -C₆alkinyl (which is optionally substituted by fluoro, chloro, bromo,cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), or represent C₁ -C₄-alkoxy (which is optionally substituted by fluoro, chloro, bromo,cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkoxy, C₁ -C₄-alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl), orrepresent C₁ -C₄ -alkylthio (which is optionally substituted by fluoro,chloro, bromo, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄-alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl), orrepresent C₂ -C₆ -alkenyloxy (which is optionally substituted by fluoro,chloro, bromo, cyano or C₁ -C₄ -alkoxy-carbonyl), or represent C₂ -C₆-alkenylthio (which is optionally substituted by fluoro, chloro, bromo,cyano, nitro, C₁ -C₃ -alkylthio or C₁ -C₄ -alkoxy-carbonyl), C₃ -C₆-alkinyloxy or C₃ -C₆ -alkinylthio, or represent the radical --S(O)_(p)-R⁶, wherep represents the numbers 1 or 2 and R⁶ represents C₁ -C₄-alkyl (which is optionally substituted by fluoro, chloro, bromo, cyanoor C₁ -C₄ -alkoxy-carbonyl), C₃ -C₆ -alkenyl, C₃ -C₆ -alkinyl, C₁ -C₄-alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄ -alkylamino, C₁ -C₄ -alkylamino, di-(C₁-C₄ -alkyl)-amino or phenyl or represents the radical --NHOR⁷, whereR⁷represents C₁ -C₁₂ -alkyl (which is optionally substituted by fluoro,chloro, cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkyl-carbonyl, C₁ -C₄-alkoxy-carbonyl, C₁ -C₄ -alkylaminocarbonyl or Di-(C₁ -C₄-alkyl)-amino-carbonyl), or represents C₃ -C₆ -alkenyl (which isoptionally substituted by fluoro, chloro or bromo), C₃ -C₆ -alkinyl, C₃-C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₂ -alkyl or phenyl-C₁ -C₂-alkyl (which is optionally substituted by fluoro, chloro, nitro, cyano,C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-carbonyl), or representsbenzhydryl or represents phenyl (which is optionally substituted byfluoro, chloro, nitro, cyano, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄-alkoxy, C₁ -C₂ -fluoroalkoxy, C₁ -C₄ -alkylthio, trifluoromethylthio orC₁ -C₄ -alkoxy-carbonyl), R⁴ and/or R⁵ additionally represent phenyl orphenoxy, or represent C₁ -C₄ -alkylcarbonylamino, C₁ -C₄-alkoxycarbonylamino, C₁ -C₄ -alkylamino-carbonyl-amino or di-(C₁ -C₄-alkyl)-amin-carbonylamino, or represent the radical --CO--R⁸, whereR⁸represents hydrogen,-C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy,C₃ -C₆ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₁ -C₄ -alkylthio, C₁ -C₄-alkylamino, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl-amino ordi-(C₁ -C₄ -alkyl)-amino (which are optionally substituted by fluoroand/or chloro), R⁴ and/or R⁵ additionally represent trimethylsilyl, C₁-C₄ -alkylsulphonyloxy or di-(C₁ -C₄ -alkyl)-aminosulphonylamino orrepresent the radical --CH═N--R⁹, whereR⁹ represents optionally fluoro-,chloro-, cyano-, carboxyl-, C₁ -C₄ -alkoxy-, C₁ -C₄ -alkylthio-, C₁ -C₄-alkylsulphinyl- or C₁ -C₄ -alkylsulphonyl-substituted C₁ -C₆ -alkyl, orrepresents optionally fluoro- or chloro-substituted benzyl, orrepresents optionally fluoro- or chloro-substituted C₃ -C₆ -alkenyl orC₃ -C₆ -alkinyl, or represents optionally fluoro-, chloro-, bromo-, C₁-C₄ -alkyl-, C₁ -C₄ -alkoxy-, trifluoromethyl-, trifluoromethoxy- ortrifluoromethylthio-substituted phenyl, or represents optionally fluoro-and/or chloro-substituted C₁ -C₆ -alkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆-alkinyloxy or benzyloxy, or represents amino, C₁ -C₄ -alkylamino,di-(C₁ -C₄ -alkyl)-amino, phenylamino, C₁ -C₄ -alkyl-carbonylamino,C_(l) -C₄ -alkoxycarbonylamino or C₁ -C₄ -alkyl-sulphonylamino orrepresents optionally fluoro-, chloro-, bromo- or methyl-substitutedphenylsulphonylamino,and also R³ represents the radical ##STR476## inwhich R¹⁰ represents hydrogen or C₁ -C₄ -alkyl,R¹¹ and R¹² are identicalor different and represent hydrogen, fluoro, chloro, bromo, mtro, cyano,C₁ -C₄ -alkyl (which is optionally substituted by fluoro and/or chloro),C₁ -C₄ -alkoxy (which is optionally substituted by fluoro and/orchloro), carboxyl, C₁ -C₄ -alkoxy-carbonyl, dimethylaminocarbonyl, C₁-C₄ -alkylsulphonyl or di-(C₁ -C₄ -alkyl)-aminosulphonyl;and also R³represents the radical ##STR477## in which R¹³ and R¹⁴ are identical ordifferent and represent hydrogen, fluoro, chloro, bromo, nitro, cyano,C₁ -C₄ -alkyl (which is optionally substituted by fluoro and/or chloro)or C₁ -C₄ -alkoxy (which is optionally substituted by fluoro and/orchloro)or the sodium salt and the potassium, magnesium, calcium,ammonium, C₁ -C₄ -alkyl-ammonium, di-(C₁ -C₄ -alkyl)-ammonium, tri-(C₁-C₄ -alkyl)-ammonium, tetra-(C₁ -C₄ -alkyl)-ammonium, tri-(C₁ -C₄-alkyl)-sulphonium, C₅ - or C₆ -cycloalkyl-ammonium and di(C₁ -C₂-alkyl)-benzyl-ammonium salt of the compounds of the formula (I).
 2. Acompound of the formula (I) according to claim 1 whereinQ¹ representsoxygen or sulphur, Q² represents oxygen or sulphur, R¹ represents ineach case optionally fluoro-, chloro-, cyano-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,or represents in each case optionally fluoro-, chloro-, orbromo-substituted propenyl, butenyl, propinyl or butinyl, or representsmethoxy, ethoxy, n- or i-propoxy or represents allyloxy, or representsmethylamino, ethylamino, n- or i-propylamino, n-, i-, s- ort-butylamino, dimethylamino or diethylamino, or represents in each caseoptionally fluoro-, chloro-, bromo-, methyl- or ethyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or representsin each case optionally fluoro-, chloro-, bromo-, cyano-, methyl-,tri-fluoromethyl- or methoxy-substituted benzyl or phenyl, R² representsin each case optionally fluoro- and/or chloro-, methyl- and/orethyl-substituted oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl,tetrahydrothienyl, oxetanylmethyl, thietanylmethyl, furylmethyl,tetrahydrofurylmethyl, thienylmethyl or tetrahydrothienylmethyl, and R³represents the radical ##STR478## in which R⁴ represents fluoro, chloro,bromo, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy,n- or i-propoxy, n- or i-butoxy, difluoromethoxy, trifluoromethoxy,2-chloro-ethoxy, 2,2,2-trifluoro-ethoxy, 1,1,2,2-tetrafluoro-ethoxy,1,1,2,2,2-pentafluoro-ethoxy, 2-methoxy-ethoxy, methylthio, ethylthio,n- or i-propylthio, n- or i-butylthio, 2-fluoro-ethylthio, allyloxy,propargyloxy, methylsulphinyl, ethylsulphinyl, methylsulphonyl,ethylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl,N-methoxy-N-methyl-aminosulphonyl, phenyl, phenoxy, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, andR⁵ represents hydrogen,fluoro, chloro, bromo methyl, ethyl, n- or i-propyl, trifluoromethyl,methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy,methylthio or ethylthio;and also R³ represents the radical ##STR479## inwhich R¹⁰ represents hydrogen,R¹¹ represents fluoro, chloro, bromo,methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy,methoxycarbonyl, ethoxycarbonyl, methylsulphonyl ordimethylaminosulphonyl, and R¹² represents hydrogen.
 3. The compound4-cyclopropyl-5-(3-oxetanyl-oxy)-2-(2-trifluoromethylphenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one.4. An herbicidal composition comprising an herbicidally effective amountof a compound according to claim 1 and an inert carrier.
 5. A method ofcontrolling unwanted vegetation which comprises applying to suchvegetation or to a locus from which it is desired to exclude suchvegetation an herbicidally effective amount of a compound according toclaim 1.